A Helpful Guide to Failure in Philanthropy. Use Carefully.

A Helpful Guide to Failure in Philanthropy. Use Carefully.

If you try to fail...and succeed, what have you done? — Phil Proctor

Let me start with a confession.

Recently, at a conference on building communities online, I was asked to discuss the biggest mistake I had made in social media. I was last in line on the panel so I had time to think, but I couldn't come up with anything other than sweat rings under my arms and an urge to wet myself. When my turn came, I had nothing. Zip. An empty plate. I failed at failure. If you too have faced this problem, I'm here to help. I want to offer my handbook to failing at philanthropy. First, an explanation.

For the most part, foundations tend to be a cautious lot. We hold lots and lots of meetings. Pile on layers and layers of review and approvals. Solicit opinions from everyone. "Let me just check with that guy waiting for a bus over there. The one wearing only one shoe. He might have some insight I missed."

When we do fail, we generally keep it to ourselves. Smarter people than me have offered explanations for this phenomenon. Most recently, Pittsburgh Foundation president Grant Oliphant, Robert Wood Johnson Foundation chief learning officer Bob Hughes, and Robert Giloth and Susan Gewirtz of the Annie E. Casey Foundation (who wrote Philanthropy and Mistakes: An Untapped Resource) offered their insights. While there are a few "good" reasons like protecting grantees, we all know the main explanation comes down to embarrassment (and ego). Few people are comfortable admitting failure. I want to add one more possibility to the literature. Perhaps foundation staff members don't know how to fail.

I don't mean to imply that we don't fail. We fail all the time. Sometimes in little ways. Sometime we go down in an impressive conflagration of failures. (See the latest edition of the Robert Wood Johnson Foundation anthology To Improve Health and Health Care for several case studies of programs that "seemed like a good idea at the time.") No, maybe the problem is that we don't know how to fail in a good way. Failing with style. Failure as success.

So, always wanting to be helpful, I offer my four steps to failing well based largely on some things I have learned working in social media.

Fail small. Social media expert Clay Shirky, author of Here Comes Everybody, warned recently about foundation staffers who claim to be working on a grant that will change the nature of life as we know it (or something equally ambitious). His advice is to lock that staff member out of the building until he or she comes back with a bunch of smaller ideas that might lead to the big one. Why? Because when an idea is that audacious, failure is out of the question (and probably assured). It's akin to the Hollywood blockbuster that has five screenwriters and is on its third director but won't die because the studio already has too much invested. Michael Organ, who headed online advertising for Barack Obama's presidential campaign, says his goal from the beginning was to fail in small ways eight out of ten times. He calls it microfailure. So here is my advice: Think big (that's important), but embrace microfailure. Look at all of your work as an experiment a pilot and plan upfront for several review points along the way that allow you to correct your course or exit altogether. First drafts are rarely your best work. It is the thousand little edits and mid-course corrections that create excellence.

Fail publicly. There is a whole world of wisdom out there, and it has become easier and easier to tap into it. Put your thoughts and ideas out for feedback early and often, don't worry that they may still feel half-baked. Don't be afraid to publicly ask for help. It is better to find out early that you are off track than when you have a full head of steam. There are plenty of people who can redirect you. Plenty of people with good ideas. Plenty of people besides the usual suspects.

Fail to win. Learn from mistakes. Turn them into successes. One of the stories in the RWJF anthology mentioned above concerns the foundation's efforts to improve the care of dying hospital patients. Clearly, it was a noble cause, but a formal evaluation of one of the first major efforts a $31 million program called SUPPORT funded between 1988 and 1996 found that little had been accomplished. The foundation could have walked away. Instead, then-president Steve Schroeder encouraged the program officer to take a careful look, gather the lessons learned, and try again. He reasoned that the goal was too important to not keep trying. The result was a $170 million effort that is credited with building the field of palliative care. Such an accomplishment might not have happened without an honest assessment of what had failed the first time out, and the drive to learn from it.

Fail proudly. Share your mistakes with gusto. Think of my buddy Bill who couldn't wait to tell everyone about the blind date who jumped out of his car as he was pulling up to her apartment building at the end of the evening. "Dude, the car was still moving." Smart failures are a badge of honor. You took a risk. You lost. You learned something. Your teachers and parents told you that the best way to learn was by making mistakes (then promptly asked, "What were you thinking?"). They were right about the first part. You remember the mistakes. They stay with you. Take calculated risks. If they don't turn out, that's okay. Share what you learned, and share the fact that you tried and it didn't work. If you are a manager, celebrate your staff's failures. Take everyone out bowling for the day. Discuss mistakes openly at the weekly meeting in an educational way (and without criticism or finger pointing). It will encourage others to do the same. It will drag failure out of the back alleys and into the light of day at your organization.

One last piece of advice. If you fail, and others with sour faces don't see it as the triumph it truly is and need a little encouragement to take some risks as well, feel free to share with them the following quote from Theodore Roosevelt:

"Far better it is to dare mighty things, to win glorious triumphs even though checkered by failure, than to rank with those poor spirits who neither enjoy nor suffer much because they live in the gray twilight that knows neither victory nor defeat."

Maybe it will work. Maybe it won't. Take a chance. Nobody wants to live in the gray twilight.

Larry Blumenthal is director of social media strategy for the Robert Wood Johnson Foundation. He blogs and tweets (@lblumenthal) regularly about philanthropy and social media.